Article
Chemistry, Multidisciplinary
Xiao-Bing Lan, Zongren Ye, Chenhui Yang, Weikang Li, Jiahao Liu, Ming Huang, Yan Liu, Zhuofeng Ke
Summary: This study presents a tungsten-catalyzed N-alkylation reaction using primary alcohols with anilines via BH/HA, demonstrating the tolerance of various functional groups, including challenging substrates with sterically hindered substituents or heteroatoms. Mechanistic insights based on experimental and computational studies are provided.
Article
Chemistry, Organic
Jiang Nan, Jiacheng Yin, Xue Gong, Yan Hu, Yangmin Ma
Summary: The novel conversion pattern with vinylene carbonate involves using the vibrant reagent as a difunctional coupling partner for the C-H annulation of free anilines. This approach allows for the rapid construction of synthetically versatile 2-methylquinoline derivatives with excellent functionality tolerance from commercially available substrates.
Article
Chemistry, Organic
Yuanyuan Lu, Huining Chai, Kun Yu, Chaonan Huang, Yujie Li, Jinyu Wang, Jiping Ma, Weiqiang Tan, Guangyao Zhang
Summary: A highly selective and reusable MOF catalyst was designed for the direct N-alkylation of amines with alcohols. This catalyst outperformed its homogeneous analogues and remained effective for at least 4 cycles without significant decrease in the yield of the target product.
Article
Chemistry, Organic
Weiqiao Lan, Jiatong Zhu, Buweihailiqiemu Abulaiti, Genyuan Chen, Zhihao Zhang, Nan Yan, Jie-Ping Wan, Xiaomei Zhang, Lihua Liao
Summary: An efficient zinc-catalyzed amination reaction has been developed for the para-selective amination of free anilines and free phenols with quinoneimides, leading to C-N bond formation via a 1,6-addition pathway. This protocol not only offers a promising approach for constructing structurally diverse p-phenylenediamine compounds with excellent yields, but also extends the application of the quinoneimide-involved 1,6-addition reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhi Zhang, Jing-Tong Deng, Jia-Yi Feng, Jin-Yan Liang, Xue-Tao Xu, Jin-Bao Peng
Summary: A palladium-catalyzed annulation of o-iodo-anilines with propargyl alcohols for the synthesis of substituted quinolines has been developed. The reaction shows tolerance towards diverse functional groups under mild conditions, providing a direct access to 2,4-disubstituted quinolines from easily available starting materials. A broad range of 2,4-disubstituted quinolines were efficiently synthesized in good to excellent yields.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Swadhapriya Bhukta, Rana Chatterjee, Rambabu Dandela
Summary: A novel and efficient method for the synthesis of substituted imidazoles has been developed using the I-2-DMSO concerted system. The reactions proceed efficiently in solvent-free conditions, resulting in good yields of various substituted imidazoles. This method offers advantages such as metal- and solvent-free process, mild conditions, and easily accessible reactants.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Applied
Li-Jing Leng, De-Long Zhang, Liang Zhang, Xiao-Long Lin, Tian Cai, Jian-Ping Tan, Qun-Li Luo
Summary: We have developed a modular catalytic protocol for the synthesis of substituted phenols via the direct dehydrogenative aromatization of simple cyclohexanones in a metal-free manner. This approach offers a simple operation, low reagent cost and green conditions, making it a promising alternative strategy for the carbonyl desaturation in organic synthesis.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Hirofumi Ueda, Ryota Yamamoto, Minami Yamaguchi, Hidetoshi Tokuyama
Summary: A three-component reaction for the synthesis of substituted anilines was developed using a gold(I)-catalyzed domino reaction. The reaction involved sequential activation of two different alkynes, resulting in a variety of substituted anilines. The utility of the aniline products was further demonstrated by derivatization to substituted benzoxazines.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Dengke Li
Summary: A general and straightforward iodine-catalyzed oxidative dehydrogenation system has been investigated for the synthesis of N-heteroarenes from saturated five and six-membered N-heterocycles. This system allows for the metal-free, additive-free, and external-oxidant-free synthesis of indole, (iso)quinoline, and beta-carboline analogues with moderate to good yields and broad functional group compatibility. The use of DMSO as both solvent and oxidant source in the transformation has been supported by preliminary mechanistic investigations. These synthetic strategies can be efficiently utilized for the elaboration of natural products.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Changpeng Chen, Liang Ling, Meiming Luo, Xiaoming Zeng
Summary: The research described a cost-effective and simple method for amidation of commercially available esters with anilines catalyzed by chromium, providing access to amides. This method has the potential to be applied in pharmaceutical and agrochemical chemistry fields.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2021)
Article
Chemistry, Organic
Amardeep Ramprasad Jadhao, Sanjay Subhash Gaikwad
Summary: A facile and sustainable copper-catalyzed thiolation method has been developed to efficiently construct benzylic thioethers under mild reaction conditions. This approach avoids the use of commonly employed thiolation reagents, making it an attractive method for benzylic thioether synthesis due to the commercial availability of base and reagents, broad substrate scope, and convenient reaction procedure.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Biquan Xiong, Shipan Xu, Weifeng Xu, Yu Liu, Limin Zhang, Ke-Wen Tang, Shuang-Feng Yin, Wai-Yeung Wong
Summary: A simple and efficient method for the silver-catalyzed regioselective 1,6-hydroarylation of para-quinone methides (p-QMs) with anilines and phenols has been established. It does not require pre-protection and is well-tolerated, giving moderate to good yields of the corresponding products. This method also allows for the synthesis of modified natural products.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Wenqi Zhao, Feng Zhang, Guo-Jun Deng
Summary: An iodine-promoted divergent thiolation of unprotected anilines with thiols has been described in this study. The combinational use of I-2 and DMSO played a crucial role in achieving this transformation without the need for a metal catalyst and strong oxidants, providing well-controlled reaction selectivity. The method offers an efficient protocol for constructing C-S and C-I bonds from C-H bonds under mild reaction conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Luyun Zhang, Yingtang Ning, Baijun Ye, Tong Ru, Fen-Er Chen
Summary: This study achieves the hydroaminomethylation of various vinyl arenes with anilines using water as the reaction media and rhodium catalyst. The water-soluble diphosphine ligands derived from bis(2-(diphenylphosphaneyl)ethyl)amides are used to facilitate the reaction. The methodology shows a wide scope of substrates and high selectivities, resulting in good yields of N-(2-phenylpropyl)anilines. Mechanistic studies reveal the imine hydrogenation reactivity of the catalysts through competition experiments and isotope labeling.
Article
Chemistry, Organic
Yuxin Ding, Renchao Ma, Yongmin Ma
Summary: A solvent-dependent I-2-catalyzed chemoselective reaction has been developed for the synthesis of benzimidazoles and 1,3,5-triarylbenzenes, showing high selectivity and efficiency.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Analytical
Xiurong Zhai, Shuai Li, Yukun Wang, Siyu Cao, Wen Sun, Mingzhu Liu, Guojiang Mao, Bingqiang Cao, Hua Wang
Summary: A magnet-renewable electroanalytical strategy has been developed for monitoring hydrogen sulfide (H2S) in aquaculture freshwater systems using magnetic Fe3O4-loaded silver metal-organic framework (Fe3O4@Ag-MOF). The method exhibits sensitive and stable signals with rational signal decline in the presence of H2S. The electrodes can be easily renewed for immobilization of Fe3O4@Ag-MOF probes, facilitating detection in aquaculture freshwater samples.
ANALYTICA CHIMICA ACTA
(2022)
Article
Chemistry, Multidisciplinary
Xuehao Li, Wenwen Cui, Qirong Deng, Xiuyan Song, Jian Lv, Daoshan Yang
Summary: An efficient and environmentally friendly method for synthesizing S-alkyl dithiocarbamates using visible light has been developed. The reaction has a broad substrate scope and good functional group tolerance in water. Importantly, no external photocatalyst is needed, making this method highly promising for applications in pharmaceutical and sulfur chemistry.
Article
Chemistry, Organic
Xuan Li, Min Jiang, Xiaolong Zhu, Xiuyan Song, Qirong Deng, Jian Lv, Daoshan Yang
Summary: The development of a new copper-based catalyst for visible-light promoted Sonogashira coupling reactions has been successful, resulting in various substituted alkynes from simple sulfonium salts. This study broadens the limited strategies of copper photocatalysts in organic transformations.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Xiaolong Zhu, Min Jiang, Xuan Li, Enjie Zhu, Qirong Deng, Xiuyan Song, Jian Lv, Daoshan Yang
Summary: The paper describes a new, efficient, metal-free organic photoredox-catalyzed direct alkylation method using alkylsulfonium salts as reagents through a desulfurization strategy under mild conditions. This inexpensive and efficient organic photoredox-catalyzed method provides a new and useful strategy for constructing various biologically interesting heteroarenes in synthetic and pharmaceutical chemistry, while expanding the scope of limited sulfonium salt photochemistry.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Man Wang, Ming Li, Long Zhang, Ran Song, Daoshan Yang, Jian Lv
Summary: Photoredox catalysis involving Ir-III in combination with DABCO as a dual hydrogen-bonding donor and organic base can enable the direct gamma-C(sp(3))-H activation of saturated alpha-keto esters, leading to the synthesis of various 4-indolyl substituted 2-hydroxy-3-enoic acid esters. This method offers high yields and high enantioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Analytical
Chunxian Zhang, Shuai Li, Zhiqiang Duan, Qin Li, Mengxuan Zhao, Yulong Chen, Xiurong Zhai, Guojiang Mao, Hua Wang
Summary: Water-soluble non-conjugated polymer dots were synthesized using hyperbranched polyethyleneimine and dihydroxybenzaldehyde for the first time. These polymer dots exhibited strong green fluorescence in aqueous media and could be quenched by MnO2 nanosheets and restored by thiocholine. A highly selective fluorimetric method for detecting organophosphorus pesticides was developed based on these characteristics.
ANALYTICA CHIMICA ACTA
(2022)
Article
Chemistry, Analytical
Luping Feng, Lixiang Zhang, Su Chu, Sheng Zhang, Xi Chen, Yushuang Gong, Zhongling Du, Guojiang Mao, Hua Wang
Summary: A nanozyme with a 2D/1D heterostructure, SWCNTs@MoS2, was successfully fabricated and demonstrated improved peroxidase-like catalysis, along with selective detection of glutathione (GSH). A colorimetric method based on SWCNTs@MoS2 was proposed for quantitative analysis of GSH, showing potential for extensive applications in clinical laboratory settings. This study opens up possibilities for designing various nanozymes with enhanced catalytic activity.
ANALYTICA CHIMICA ACTA
(2022)
Article
Chemistry, Organic
Wenwen Cui, Xufeng Li, Guoju Guo, Xiuyan Song, Jian Lv, Daoshan Yang
Summary: In this study, a copper-catalyzed blue-light-induced free radical ring-opening reaction of sulfonium salts with dichalcogenides was developed. The method utilizes an inexpensive copper catalyst and has a broad substrate scope, allowing for the high-yield synthesis of alkyl chalcogenides. This reaction presents a novel ring-opening model for sulfonium salts, breaking the limitation of only nucleophilic ring-opening reactions to form C-heteroatom and C-C bonds.
Article
Chemistry, Applied
Ran Song, Caiqi Zhuo, Wen Si, Xiaoying Wu, Tianyi Guan, Daoshan Yang, Jian Lv
Summary: A metal-free method for synthesizing diarylmethylamines was developed using a 1,6-addition reaction of 1-aminobenzotriazole with p-quinone methides catalyzed by triphenylcarbenium tetrafluoroborate. The diarylmethylamines were obtained in moderate to good yields (up to 84%) under mild conditions, and showed unchanged activity after 6 reuses.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Analytical
Chenchen Xu, Qingqing Liu, Su Chu, Pan Li, Fengxiang Wang, Yanmei Si, Guojiang Mao, Choufei Wu, Hua Wang
Summary: A microdots array-based fluoremetric method with superwettability profile was developed for simultaneous and separate detection of Fe3+ and Cu2+ ions in red wine samples. The fluoremetric microdots array platform was obtained by designing a wettable micropores array and immobilizing fluorescent probes in it. The platform enabled the accumulation of targeting ions without tedious preprocessing and reduced cross-contamination. The feasibility of simultaneous and separate detection of Fe3+ and Cu2+ ions in red wine samples was demonstrated.
ANALYTICA CHIMICA ACTA
(2023)
Article
Chemistry, Organic
Hao Xu, Xufeng Li, Yuzheng Dong, Shuangran Ji, Junze Zuo, Jian Lv, Daoshan Yang
Summary: An efficient strategy for the preparation of aryl phosphonates has been demonstrated via a blue-light-promoted single electron transfer process of an EDA complex. The method enables the construction of aryl phosphonates through the indirect C-H functionalization of arenes, leading to good to excellent yields of substituted aryl phosphonates and the recovery and reuse of the byproduct thianthrene. This approach has potential application value in drug discovery and development.
Article
Chemistry, Organic
Yuan Tian, Mengdie Tang, Changshuo Lian, Ran Song, Daoshan Yang, Jian Lv
Summary: The diastereo- and enantioselective oxa-Nazarov cyclization-Michael addition of conjugated 1,2-diketones was successfully achieved through asymmetric binary-acid catalysis using chiral phosphoric acid and FeBr3, giving the corresponding chiral 3(2H)-furanones in good yields and with high stereoselectivity (up to >95 : 5 dr and 96% ee).
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Wenwen Cui, Guoju Guo, Yifei Wang, Xiuyan Song, Jian Lv, Daoshan Yang
Summary: An efficient method has been developed for the site-selective alkylation of silyl enol ethers with arylsulfonium salts, leading to the synthesis of valuable aryl alkyl thioethers under visible light conditions. This approach enables the selective cleavage of the C-S bond in arylsulfonium salts, through copper (i) photocatalysis, to generate C-centered radicals under mild conditions. It provides a straightforward strategy to utilize arylsulfonium salts as sulfur sources for the synthesis of aryl alkyl thioethers.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Analytical
Yuchun Qiao, Yu Fang, Jizhen Shang, Xiaoting Zhao, Shuai Li, Guojiang Mao, Hua Wang
Summary: In this study, a fluorescent test strip with suppressed CRE of silver nanocluster probes coated by gelatin was successfully fabricated using vacuum-aided fast lyophilization, enabling uniform and stable probe deposition as well as sensitive quantitative analysis.
Article
Chemistry, Organic
Qiuli Yan, Wenwen Cui, Junxin Li, Guiyun Xu, Xiuyan Song, Jian Lv, Daoshan Yang
Summary: A highly efficient visible-light promoted benzylation method using riboflavin as a green photocatalyst has been developed for synthesizing C3-benzylated quinoxalin-2(1H)-one derivatives. This method offers a new approach for the synthesis of these derivatives, with potential applications in pharmaceutical and synthetic chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2022)
